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Highwood Vacation Packages

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Highwood Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Price was $506, price is now $352 per person
$352
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.

Reviewed on Nov 3, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Price was $1,182, price is now $718 per person
$718
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was $1,148, price is now $725 per person
$725
per person
Dec 16 - Dec 23
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was $947, price is now $622 per person
$622
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $756, price is now $509 per person
$509
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
I like the roof top experience. It was amazing at night. The breakfast was very good and convenient. My only gripe was parking $75 a day for valet parking and $55 self parking.

Reviewed on Nov 12, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Price was $825, price is now $565 per person
$565
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
It was a good stay and I would stay here again.

Reviewed on Nov 12, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $605, price is now $419 per person
$419
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Price was $541, price is now $382 per person
$382
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Highwood Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $756, price is now $509 per person
$509
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,182, price is now $718 per person
$718
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $947, price is now $622 per person
$622
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $825, price is now $565 per person
$565
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Highwood Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,010, price is now $627 per person
$627
per person
Feb 4 - Feb 9
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,781, price is now $1,080 per person
$1,080
per person
Jan 23 - Jan 30
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was $1,148, price is now $725 per person
$725
per person
Dec 16 - Dec 23
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,692, price is now $1,108 per person
$1,108
per person
Jan 23 - Jan 30
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, Dec 8 - Sat, Dec 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$240 Roundtrip, found 1 hour ago
$240
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Dec 8 from Los Angeles Intl. to O'Hare Intl., returning Sat, Dec 12, priced at $240 found 1 hour ago
United
Sat, Dec 19 - Wed, Dec 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$258 Roundtrip, found 1 hour ago
$258
Roundtrip
found 1 hour ago
Select United flight, departing Sat, Dec 19 from Los Angeles Intl. to O'Hare Intl., returning Wed, Dec 23, priced at $258 found 1 hour ago
Delta
Tue, Jan 5 - Tue, Jan 19
LAX
Los Angeles Intl.
MDW
Midway Intl.
$274 Roundtrip, found 20 hours ago
$274
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Jan 5 from Los Angeles Intl. to Midway Intl., returning Tue, Jan 19, priced at $274 found 20 hours ago
Delta
Mon, Nov 16 - Sun, Nov 22
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,198 Roundtrip, found 6 hours ago
$1,198
Roundtrip
found 6 hours ago
Select Delta flight, departing Mon, Nov 16 from Pudong Intl. to O'Hare Intl., returning Sun, Nov 22, priced at $1,198 found 6 hours ago